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4-Bromoquinoline → HCID 59605440, 화합물

HRID 1945757
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HRID 1945757 반응식
[CH3:1][C:2]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[S:22][C:21]3[C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:19][C:18]([Sn](CCCC)(CCCC)CCCC)=[N:17][C:16]=3[CH:15]=2)[CH2:9][CH2:8]1)([CH3:6])[C:3]([NH2:5])=[O:4].Br[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]=[CH:45][CH:44]=1>O1CCOCC1.S1C=CC=C1C([O-])=O.[Cu+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]([N:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[S:22][C:21]3[C:20]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:19][C:18]([C:43]4[C:52]5[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=5)[N:46]=[CH:45][CH:44]=4)=[N:17][C:16]=3[CH:15]=2)[CH2:11][CH2:12]1)([CH3:6])[C:3]([NH2:5])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 117359184-BromoquinolineHCID 575067302-[4-(4-Morpholin-4-yl-2-(tributylstannanyl)-thieno[3,2-d]pyrimidin-6-ylmethyl)piperazin-1-yl]isobutyramide

생성물 1

HCID 59605440HCID 59605440, 화합물수율 29%

시약·촉매·용매 3

HCID 11194830Cuprous 2-thiophenecarboxylate촉매
HCID 178418397
HCID 178418397, 화합물
촉매
HCID 312751,4-Dioxane용매

실험 절차

To a degassed mixture of 2-methyl-2-(4-((4-morpholino-2-(tributylstannyl)thieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)propanamide (235 mg, 0.339 mmol), 4-bromoquinoline (60 mg, 0.288 mmol), copper(I) thiophene-2-carboxylate (55 mg, 0.228 mmol) in dioxane (2 mL) was added Pd(PPh3)4 (17 mg, 0.014 mmol). The reaction mixture was reacted in the CEM microwave at 140° C. for 30 min. The reaction mixture was then loaded onto a Biotage Isolute SPE SCX-2 column. The column was washed with MeOH, eluted with 2 M NH3 in MeOH and further purified by RP-HPLC to give 171 (44 mg, 29%). LCMS: M+H+=532.2. 1H-NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 9.04 (s, 1H), 8.86 (d, 1H), 8.22 (d, 1H), 7.84 (t, 1H), 7.73 (t, 1H), 7.47 (s, 1H), 7.06 (s, 1H), 6.94 (s, 1H), 3.97 (m, 4H), 3.88 (s, 2H), 3.68 (m, 4H), 2.54-2.67 (m, 8H), 1.09 (s, 6H)

후처리

  1. customThe reaction mixture was reacted in the CEM microwave at 140° C. for 30 min
  2. washThe column was washed with MeOH
  3. washeluted with 2 M NH3 in MeOH
  4. customfurther purified by RP-HPLC

출처 및 근거

ORD 기록
ord-007c1f59bd4e46b6a7c89519269af8cd
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08394796B2

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